


Jim's Poker Plans

by kioseth



Category: The Office (US)
Genre: Blackmail, Gen, Humiliation, M/M, Masturbation, Strip Poker
Language: English
Status: Completed
Published: 2018-11-15
Updated: 2018-11-15
Packaged: 2019-08-23 21:16:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,677
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16626605
Author URL: https://archiveofourown.org/users/kioseth/pseuds/kioseth
Summary: Jim has been learning poker tips from Kevin to trick Dwight out of his clients. Dwight has a different idea with some high stakes. Who will be the victor?





	Jim's Poker Plans

  
The setup was too easy. Having learned a bunch of tips and tricks from Kevin, Jim considered himself somewhat of a exceptional poker player. He still lost to Kevin most of the time but was confident in his ability to win against any average player.

  
In an effort to prank and embarrass Dwight he convinced him to a game of poker after work. They started their first game with 100 bucks each and after letting Dwight win most of the hands, Jim set his trap.

"Okay Dwight. I can't keep losing money or Pam is going to kill me. Can we bet something else?"

  
Dwight shuffled the cards, not looking at Jim. "What did you have in mind, Halpert?"

  
"Clients. We could bet with our clients. At the end of the night, we transfer whatever clients we won or lost to the other person to take over."

  
Dwight laughed. "Jim, I would destroy you and take every last customer you serviced. You'd be out of a job by 6PM." He continued shuffling.

  
"Or, Dwight, are you nervous that I'll beat you and leave you with no clients?"

  
Dwight scoffed. Unknown to Jim, Dwight didn't think Halpert had a chance in hell of beating him but Dwight cared about Pam and the half of Cici that was hers. Pam had always been... nice to Dwight. Taking away Jim's financial security would ruin Pam and her daughter. No, Dwight had other plans to beat Jim and get back at him for all his pranks.

  
"No, not at all. I just don't want your money, Jim. I want your pride. I want to humiliate you like you attempt to do to me."

  
"Dwight, I don't.."

  
"No. We play and old fashioned game that originated on Schrute farms centuries ago to whittle down enemies without bloodshed. Garments Lost, Garments Gained."

  
"And what is that?" Jim asked.

  
"Simple rules. We play poker as normal but instead of chips we bet our clothes. Winner keeps their articles of clothing bet and loser hands their better articles to the winner. However you can only bet using your own clothes even if you somehow manage to win some from me."

  
"Strip poker?"

  
"Ugh, your European lineage disgusts me. Fine, call it what you want."

  
"You want to play strip poker with me? Dwight I had no idea you wanted to get me naked so badly."

  
"Jim, no, it's not that."

  
"I mean when you kept grabbing my crotch that one day I suspected, but, never truly thought you were gay since.."

  
"Jim, gross, no. I only fornicate and enjoy the genitalia of women with good posture and fertile ovaries. Let me add in."

  
Jim sits quietly with a smirk.

  
"When we finish the game, we walk out of here in whatever clothes we have left."

  
Jim cuts in, "Dwight it's like 5.30 now. By the time we're done no one will be here. Still sounds like you just want to see little Jim."

  
"Fitting you call it little."

  
"Big Jim. I mean Big Jim!" Jim coughed, not meaning to have insinuated anything.

  
"AND, Jim, we work tomorrow in the same state of dress."

  
Jim felt like he struck gold. Having Dwight come into the office naked tomorrow would certainly not sit well with anyone in the office and likely ensure his firing if not temporary suspension for insanity. Toby wouldn't let him stay for more than 10 minutes. While he didn't enjoy the idea of innocent bystanders, like his wife, potentially glimpse Dwight in a fully nude state, the temptation was rising.

  
Jim also weighed the chance that he may lose. He quickly brushed that aside but while confident he would win, there was a strong chance he would lose an article or two. Deciding that would ultimately just mean he may have to work barefoot tomorrow, Jim agreed.

  
"I'm in."

  
Dwight smiled, ear to ear. Jim assumed Dwight had the same ideas of Jim being let go once flashing the entire office with his totally large, above-average penis. "Okay then."

  
The first hand both men bet a shoe but called with garbage on both ends. Dwight got lucky with a pair of 4's though. The next hand lost Jim his other shoe too.

  
Jim thought to himself, _Okay. Not going as planned so far but I just got really unlucky here._

  
His luck turned swiftly though. The next hand he was dealt a three of a kind, 9s high but unfortunately Dwight folded. _Dammit_.

  
However the very next hand Jim got two pair, Ace high and he forced himself not to show his excitement. Dwight too seemed happy with his likely high pair and raised Jim's two socks. Jim added his shirt to the offer table and Dwight his tie.

  
When they called Jim was shocked to see 3 Kings lay down in front of Dwight. _That bitch!_

  
"Well Jimmy, I'm not sure why you would have agreed to this given how badly you were losing before.."

  
_Yeah, letting you win._ "My luck will change."

  
"Uh huh, cough up the shirt."

  
Jim unbuttoned his shirt once removed, threw it at dwight. He took his socks off as well and threw them over. Now sitting in just his undershirt, pants, and boxers Jim started to feel a bit nervous. Dwight had lost nothing.

  
Jim could walk now but he was positive his luck would turn. "You'll be naked soon," Jim challenged.

  
"Now who sounds like a homosexual?"

"No.. I.. Ugh! Just deal, Dwight."

  
Jim, cautious, was unwilling to bet for three hands and folded each time. Finally he manged to land a Straight and bet his shirt and after a raise by Dwight, _the idiot_ , his pants.

  
He laid his straight, Jack high confident Dwight would begin to get a bit colder. Yet again, for what Jim hoped and pleaded would be the last surprise of the night, Dwight laid down all spades.

  
"I think they call this a Flusher? Is that right Jim?"

  
"..How? How are you beating me? Are you cheating?"

  
"Oh, poor sportsmanship Jim. Tsk Tsk."

  
Jim ripped the cards away from Dwight and looked through them for any discrepancy in the deck, even though he knew the cards were his own. Frustrated to not find anything out of order, "I deal from now on. I don't trust you and your Beet magic."  
"Magic isn't real, Jim. Or at least not the nonsense television expects you to believe. Curses and hexes are far more alchemical."

  
Jim shuffled.

  
"Ah, Jim. Your shirt."

  
Jim rolled his eyes and set the cards down. Peeling his white shirt off his body exposed the thinner man's chest. Lightly dusted in brown hair, his chest was decently defined. Small pink nipples stood erect being exposed to the open air of the conference room.

  
He threw it, again, at Dwight and sat back down.

  
"Jimmm..."

  
"You know I know some guys you may like if you really want to get into a guys pants so badly."

  
"Ha. Ha. I'm a homosexual. Tell yourself whatever you need to as long as you hand over those trousers.

  
"Pants, Dwight! They're called pants!"

  
Jim stood back up angrily and unbuckled, unbuttoned, and unzipped his pants. They dropped to the floor and Jim stepped out of the puddle of fabric. He kicked them over to Dwight's side of the table.

  
Dwight didn't even look down but kept locked eyes with Jim. Likely imaging his winning scenario play out, but Jim was imaging the same thing. He felt it. He knew it.

  
Jim silently dealt the cards, and after exchanging three, almost fell out of his chair. A full house sat before him. He had been hoping for 3 of a kind or at least a two pair but was a pleasant surprise. He was confident he could win but unfortunately could only bet one thing. He looked down into his lap, the soft bulge of his clothed cock was at risk but this was clearly fate or whatever you want to call it.

  
He took a breath, and bet his remaining veil of his shame. And lady luck was indeed in that room. Just not on Jim's side of the table.

  
"How the fuck, Dwight?!"

  
Dwight didn't say anything, but instead just leaned back in his chair and put his hands behind his head.

  
"Fuck!" Jim cursed.

  
He stood up and paced a bit back and forth realizing what he had bet. Not just his boxers and the idea of Dwight seeming him naked, he was more-or-less fine with that, but he had agreed to now come into the office tomorrow completely naked. Andy was pretty chill but there was no way this went down any way other than him being fired.

  
"Listen, Dwight.."

  
"Nope. Drop them."

  
"Dwight, I think.."

  
"I will entertain no conversation with you until I've won what you've rightfully lost."

  
Jim threw his head back and rubbed his hands against his eyes. "Fine!" In a swift motion without thinking, Jim shucked his boxers off and tossed them to Dwight. He covered his manhood with his hands.

  
"Now Dwight, listen, about the rest of the bet."

  
"One which you fully are obligated to complete given verbal contracts are legally binding in the state of Pennsylvania."

  
"Dwight, I can't do that, you know I would be fired."

  
"I'm willing to accept that risk."

  
"Dwight, come'on, man! I wouldn't have made you go through with it. I would have just made you do something embarrassing to get out of it but I wouldn't have set you up to be fired."

  
Dwight pondered this. There was a good chance that Jim may bulk all together if Dwight pushed too hard.

  
"Okay. I have an alternative."

  
"Yes! Anything Dwight."

  
"To ensure you don't scheme against me anymore, I'm going to need some blackmail on you."

  
"I.. I don't under.."

  
"Come with me."

  
Dwight stood and opened the door to conference room. Jim hid down behind the table fearing that people may still be in even though it must be nearing 7 o'clock.

  
"No one's here Jim, get out here."

  
Not really having another option, Jim crept out of the office, peering around cautiously for any life other than he and Dwight.

  
Sit at your desk. Jim obeyed.

  
"Dwight, what do you want me to do, here?"

  
"Simple. Smile."

  
Dwight took out his phone and took a photo of Jim. "Dwight?! Come'on man, no photos!"

  
"Oh yes, Jim, photos. These will ensure you don't mess with me any more. If you do then I'll be forced to turn them over to Andy. Now let's do another one but remove your hands from your genitals. I want to make sure it's evident you're naked in the office."

  
Jim's heart raced unsure of what to do. At this point Dwight already had a pretty incriminating photo of him and so he felt obligated to go along with it. Slowly, and unsure of himself, he moved his hands away exposing his cock and balls to Dwight for the first time.

  
"Hm. Average."

  
"Very clearly above!"

  
"Perhaps; the only other penises I look at are those of donkeys and work horses and you pale by comparison."

  
"I think I'm okay with that. Will you just take the picture already."

  
Once taken, Jim got up to go grab his clothes but Dwight stopped him. "Oh no Jim, we're not done. I need a photo of you at each desk. Just in case I need to convince any particular parties you're a heinous deviant."

  
"Seriously, Dwight?"

  
"Dead serious, my compadre."

  
And so the photo shoot began, Dwight expecting more and more out of each pose at each desk. Standing with his cock on Phyllsus's phone, twerking in Stanley's chair, humping Creed's desk. Posing like a porn star on Oscar's desk while holding a picture of him and his new dog.

  
"Actually, I think it would be more funny and embarrassing if you were erect for Oscar's desk."

"What, Dwight?!"

  
"You know, because he's a homosexual! It will imply that you are too since you are aroused with a photo of him."

  
"I'm not getting hard, Dwight. I couldn't even if I tried."

  
"Well I do hope you try, or else these are being group texted right now to everyone in the office."

  
"God fucking dammit, Dwight. You're sick."

  
"Oh you have no idea, Halpert."

  
It took Jim a couple minutes and he asked Dwight to move away but finally he was able to get a boner with the help of some porn on his phone. Not his proudest erection but would suffice Dwight and his sick demands.

  
"That's above average?"

  
"Shut up Dwight?"

  
"How big do you think average is for a human, white male?"

  
"Dwight!"

  
"I'm asking you a question, Jim."

  
"5 inches. The average penis size is 5 inches."

  
"And you are?"

  
"I don't know, Dwight."

  
"Oh, you don't?" Dwight pretended to text on his phone.

  
"5 and a half! My cock is 5 and a half inches, Dwight. God!"

  
"Hm, I'm surprised Pam has stayed with you at all. Although given the size of your testicles I imagine you're quite fertile so perhaps that's your lasting quality. You're also precumming a lot which supports that."

  
Jim was stunned a bit at the reference to his balls, which he agreed are pretty big, and then looking down noticed Dwight was right and he had a glob of pre dripping down his cock.

  
"Rub it on Oscar's face a bit."

  
Jim just rolled his eyes but didn't argue knowing it would go nowhere. The photos were damning. He knew it but he was in too deep.

  
More photos were asked of him on other desks. Exposing his ass on Ryan's desk. Pretending to finger himself on Toby's. Grabbing his nipples near Kelly's.

  
Dwight seemed to have no limit for what he would ask for. That was clear when they got to Andy's office.

  
"Masturbate."

  
Jim posed pretending to do-so.

  
"No, actually masturbate. This one is special, it's going to be a video."

  
"Dwight!"

  
"Jim, it's the last one and then we're done. Then you can go home to your boring little life and we can finally put all of these pranks behind us. I need this to be sure."

  
Another eye roll, another sigh, and another big breath. Jim grasped his cock and started to stroke himself. Pre coating his hand and making an unmistakable sloshing sound.

  
"How long do you want me to do this?"

  
"Until you ejaculate. I want you to ejaculate on Andy's desk."

  
Of course he does.

  
Jim was refusing to admit it consciously, but the night of exposure had turned him on and getting in the mood was no challenge. In about two minutes he brought himself to his peak.

  
Jim threw his left hand on Andy's desk for support as he erupted onto Andy's mouse, keyboard, and desk. Rope after rope puddled before Jim's engorged cock. Jim was panting. His cock wasn't really deflating yet either. What a rush.

  
"Now lick it up."

  
"Dwight, that's actually gay! I'm not gay!"

  
"It's your own juices, amateur. It's completely natural to reclaim that protein as to not let it go to waste. Now lick it up, Halpert."

  
Maybe it was the post-climax high or the insatiable need that was bubbling up in Jim to be exposed like this and told what to do, but he obeyed. Jim honestly had never tasted his own cum but was happily surprised that it wasn't bad. His tongue lapped up large scoops of his salty but semi-sweet juice that Pam typically enjoyed. He understood why, now.

  
And in a purely business like fashion, Dwight closed his phone and walked out of the office. He grabbed his briefcase and walked out of the office.

  
Jim sat back in Andy's chair, unsure of what would happen next but in the moment not caring. He looked down at his still hard cock and took hold. He came two more times that night before cleaning up and leaving, not wasting a single drop.


End file.
